Planning a multigenerational trip: Tips from travel experts

For the past 11 years, Kathy Sudeikis has planned a yearly family reunion. Called “Nanapalooza,” the tradition began as a way to bring her six siblings and their families together to honor the memory of their mother.

Held annually near Michigan City, Indiana, the event has doubled from about 40 people in its first year to 74 last summer. Kathy’s son, “Ted Lasso” star Jason Sudeikis, ranks among those who have never missed a year of Nanapalooza — and he’s not the only one who’s committed to participating.

“One family drives from New York ... Another cousin had her baby induced so she could bring the baby,” Kathy Sudeikis said.

Sudeikis works for Acendas Travel, a Kansas City-based travel management company, so she has extensive experience in the industry and is the de facto leader of Nanapalooza. But not all multigenerational trips and reunions go well, with families sometimes arguing over details such as when to travel and how to split bills. That’s why Heidi Durflinger, president of EF Go Ahead Tours in Cambridge, Massachusetts, recommends hiring a tour director.

“The tour director is there from start to finish, so they get to know everyone’s interests,” Durflinger said. “They’re pros at handling group dynamics.”

You can also, of course, plan it on your own.

SELECTING DATES

Sometimes, the hardest part of trip planning can be settling on dates.

“It’s just never going to work perfectly for everyone,” Sudeikis said. “There’s always someone whose kid has band camp that week.”

To avoid such drama, Sudeikis advised tying trips to important family dates. With Nanapalooza, it’s the anniversary of the death of her mother.

DECIDING WHERE TO GO

To help agree on a location, Durflinger recommended considering family heritage. Her company recently organized a family reunion in an Italian village where the family’s ancestors were from.

Nanapalooza’s location, meanwhile, was selected because one family owns a waterfront property on Lake Michigan, which provides a convenient base for most meals and activities. The families book their lodging nearby.

PLANNING ACTIVITIES

Cruises or all-inclusive resorts can simplify family vacations by offering meals and planning activities for everyone. For example, at Vista Verde Guest Ranch, an all-inclusive dude ranch in Clark, Colorado, guests choose activities from a preselected list, then everyone regroups in the main lodge for meals.

Sudeikis sends out a food chart in advance to reunion attendees. Then, each of the seven siblings picks a single meal to prepare for the entire group.

PAYING FOR THE TRIP

At Nanapalooza, each family rotates supplying the entire group’s dinner. Frugal families could cook, while another family might pay for takeout.

And don’t overlook a professionally organized tour just because participants are in different financial brackets. Durflinger said a tour may come out cheaper since they can secure discounted rates for large groups.